CN108774542A - A kind of method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product - Google Patents
A kind of method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product Download PDFInfo
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- CN108774542A CN108774542A CN201810725218.1A CN201810725218A CN108774542A CN 108774542 A CN108774542 A CN 108774542A CN 201810725218 A CN201810725218 A CN 201810725218A CN 108774542 A CN108774542 A CN 108774542A
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- Prior art keywords
- phenolic compound
- hydrogenation deoxidation
- hydro carbons
- lignin depolymerization
- ferrous
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- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 19
- 229920005610 lignin Polymers 0.000 title claims abstract description 19
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 18
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 18
- 150000002989 phenols Chemical class 0.000 title claims abstract description 18
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 17
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 12
- 229910001448 ferrous ion Inorganic materials 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000001509 sodium citrate Substances 0.000 claims description 5
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 229960001867 guaiacol Drugs 0.000 claims description 3
- 239000002105 nanoparticle Substances 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229960002089 ferrous chloride Drugs 0.000 claims description 2
- 239000011790 ferrous sulphate Substances 0.000 claims description 2
- 235000003891 ferrous sulphate Nutrition 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- OQUFOZNPBIIJTN-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;sodium Chemical compound [Na].OC(=O)CC(O)(C(O)=O)CC(O)=O OQUFOZNPBIIJTN-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical class C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 7
- 229910052742 iron Inorganic materials 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 anethene Chemical compound 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical class CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910003294 NiMo Inorganic materials 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 241000255964 Pieridae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- ROLPKBACLNPIJH-UHFFFAOYSA-N iron;phenol Chemical compound [Fe].OC1=CC=CC=C1 ROLPKBACLNPIJH-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/06—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation
- C10G1/065—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation in the presence of a solvent
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/745—Iron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
- B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the methods that mononuclear phenolic compound hydrogenation deoxidation in a kind of Catalytic lignin depolymerization product prepares hydro carbons, using Nanoscale Iron as catalyst, phenolic compound can efficiently be converted into hydro carbons chemicals, and it is catalyst abundant raw material, cheap, preparation condition is mild, preparation method is simple, catalytic activity is excellent, hydrogenation deoxidation is efficient, have it is at low cost, efficiency is higher, the advantages of can be in large-scale application.
Description
Technical field：
The present invention relates to biomass liquid fuels and chemicals preparing technical field, and in particular to a kind of Catalytic lignin solution
The method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in poly- product.
Background technology：
Lignin is the chief component of biomass, is the Main By product of cellulosic ethanol industry and paper industry,
Due to being not fully utilized, becomes environmental contaminants, very big pressure is brought to environment.Therefore, lignin efficiently turns
The utilization rate of liquid fuel or chemicals to raising biomass carbon resource is turned to, the economy for improving biomass utilization technologies has
Significance.Usually, mononuclear phenolic platform chemicals are obtained by catalytic degradation, then lignin may be implemented in hydrogenated deoxidation
Transformation to HC fuel or chemicals.
The catalyst type of phenolic compound hydrogenation deoxidation is more.Wherein study earlier be with sulphided state metal be activity
The bifunctional catalyst of phase is (such as the MoS of load2、NiMoS2、CoMoS2Equal catalyst).It is easy during such catalyst reaction
Coking deactivation.In addition, having to last for providing certain density H in reaction system2S avoids catalyst activity to maintain sulphided state
The loss at center.H2Being introduced into for S causes to introduce a large amount of element sulphurs in product.
There is the noble metals such as Pd, Pt, Ru, Rh, Ir very high catalytic hydrogenation activity can be selected under mild hydrogenolytic conditions
The fracture lignin and its model compound of selecting property, by feed degradation at monomer, dimer and oligomer compounds.For example,
The lower Spruce lignin selectivity of Pd, Pt, Ru and Pd effect of Al-SBA-15 loads is decomposed into 4- ethyl -phenols.However,
Under the conditions of harsh lignin degradation, such catalyst is very unstable, is easy inactivation；In addition, such noble metal catalyst
It is expensive, it is not appropriate for carrying out large-scale industrial production.
In addition to noble metal, transition state and other B metals are also anti-in lignin depolymerization and lignin derivative hydrogenation deoxidation
It answers middle in the presence of activity.As the oxide of molybdenum, nitride and carbide etc. are used for wood if the 1980s as catalyst
The hydrogenation deoxidation of quality and phenols model compound reacts.The bimetallics such as the metals such as transiting state metal Co, Ni and CoMo, NiMo are urged
Agent is also very common in the hydrogenation deoxidation reaction of phenolic compound.
Invention content：
The object of the present invention is to provide mononuclear phenolic compound hydrogenation deoxidations in a kind of Catalytic lignin depolymerization product to prepare
The method of hydro carbons, using Nanoscale Iron as catalyst, phenolic compound can efficiently be converted into hydro carbons chemicals, and catalysagen
Material is abundant, cheap, and preparation condition is mild, preparation method is simple, and catalytic activity is excellent, hydrogenation deoxidation is efficient, have at
This is low, efficiency is higher, the advantages of can be in large-scale application.
The present invention is achieved by the following technical programs：
A kind of method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product, this method with
The higher phenol of content, methyl phenyl ethers anisole, guaiacol, benzyl oxide, diphenyl ether, anethene, 4- benzyloxy benzene in lignin depolymerization product
The mononuclear phenolic compounds such as phenol, benzofuran are raw material, and normal octane is for solvent by raw material under the action of nanometer iron powder catalyst
It carries out hydrogenation deoxidation reaction and is converted into hydrocarbon products, reaction temperature is 260-340 DEG C, reaction time 1-20h, reaction system
Middle Hydrogen Vapor Pressure is 2.0-6.0MPa；The nanometer iron powder catalyst is prepared by solution phase chemical reduction in room temperature environment, tool
Preparation is as follows：The NaOH solution and sodium citrate that pH value is 8-10, stirring is added, stir speed (S.S.) 600rpm is passed through
Nitrogen forms inert protective atmosphere, and NaBH is added dropwise successively4With ferrous ion (Fe2+) solution, stir 30min after, detached with magnet
Obtain the nanoparticle catalyst of black；Wherein NaBH4Be less than 2 with the molar ratio of ferrous ion, sodium citrate be it is ferrous from
0.1-0.15 times of sub- molal quantity.
The ferrous ions soln preferably ferrous sulfate or solution of ferrous chloride.
Beneficial effects of the present invention are as follows：Nanometer iron powder catalyst abundant raw material, cheap, preparation condition is mild, system
Preparation Method is simple, and catalytic activity is excellent, hydrogenation deoxidation is efficient, reusable, under nanometer iron powder catalyst action, phenols
Compound can efficiently be converted into hydro carbons chemicals.
Specific implementation mode：
It is the further explanation to the present invention below, rather than limiting the invention.
Embodiment 1：The preparation of catalyst
NaOH solution and the sodium citrate that pH value is 9, stirring are added in three-necked flask, stir speed (S.S.) 600rpm leads to
Enter nitrogen and form inert protective atmosphere, 0.2mol L are added dropwise successively-1NaBH4With 0.5mol L-1Ferrous ion (Fe2+) solution,
After stirring 30min, the nanoparticle catalyst of black is obtained with magnet separation；Wherein NaBH4With the body of ferrous ions soln
Product is than being 1：1, sodium citrate is 0.15 times of ferrous ion molal quantity.
Embodiment 2：
The 2.0g nanometer iron powders that embodiment 1 is prepared, the lignin depolymerization phenol product and 30.0ml of 1.0g are just
Octane is put into 100ml autoclaves, is sealed reaction kettle, is used H2It replaces gas reactor 5 times, fills H2It is pressurized to 4.0MPa.It opens
Agitating paddle (700rpm) is opened, reaction kettle is warming up to 300 DEG C with the rate of heat addition of 3 DEG C/min, starts clock reaction.Reaction time
For 8h.Hydrocarbon product yield is 94%.
Embodiment 3-15：
Reference implementation example 2, the difference is that reaction temperature, pressure and time difference, referring specifically to table 1：
Table 1
Embodiment 16-22：Nanometer iron powder catalyst Pyrogentisinic Acid's hydrogenation deoxidation prepares the repeatability reaction of hydrocarbon product
Reference implementation example 2, catalyst reuses number and reaction result is shown in Table 2.
Table 2
| Embodiment | Catalyst utilizes number | Hydro carbons yield (%) |
| 16 | 1 | 94 |
| 17 | 2 | 94 |
| 18 | 3 | 93 |
| 19 | 4 | 87 |
| 20 | 5 | 79 |
| 21 | 6 | 72 |
| 22 | 7 | 70 |
Embodiment 23-29：Different phenolic compound hydrogenation deoxidations prepare the reaction of hydrocarbon product
Reference implementation example 2, the difference is that being other phenolic compounds, reaction result is shown in Table 3.
Table 3
Comparative example 1-2：
Comparative example 1：
Reference implementation example 2, the difference is that catalyst is iron, as a result referring to table 4.
Comparative example 2:
Reference implementation example 23, the difference is that catalyst is catalyst disclosed in CN105461498B, as a result referring to table
4.
Table 4
| Comparative example | Reactant | Catalyst | Hydro carbons yield (%) |
| 1 | Phenol | Iron | 13 |
| 2 | Guaiacol | Fe/Ni/HY | 26.53 |
Claims (2)
1. a kind of method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product, feature exist
In for this method using mononuclear phenolic compound in lignin depolymerization product as raw material, normal octane is solvent, in nanometer iron powder catalyst
Under the action of raw material be subjected to hydrogenation deoxidation reaction be converted into hydrocarbon products, reaction temperature is 260-340 DEG C, and the reaction time is
1-20h, Hydrogen Vapor Pressure is 2.0-6.0MPa in reaction system；The nanometer iron powder catalyst passes through liquid phase in room temperature environment
It learns reduction method to prepare, specific preparation method is as follows：The NaOH solution and sodium citrate that pH value is 8-10, stirring, stirring speed is added
Rate is 600rpm, is passed through nitrogen and forms inert protective atmosphere, NaBH is added dropwise successively4And ferrous ions soln, after stirring 30min,
The nanoparticle catalyst of black is obtained with magnet separation；Wherein NaBH4It is less than 2 with the molar ratio of ferrous ion, citric acid
Sodium is 0.1-0.15 times of ferrous ion molal quantity；The mononuclear phenolic compound is selected from phenol, methyl phenyl ethers anisole, guaiacol, benzyl
Any one of ether, diphenyl ether, anethene, 4- benzyloxy phenols, benzofuran.
2. mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product according to claim 1
Method, which is characterized in that the ferrous ions soln is ferrous sulfate or solution of ferrous chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810725218.1A CN108774542A (en) | 2018-07-04 | 2018-07-04 | A kind of method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product |
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|---|---|---|---|
| CN201810725218.1A CN108774542A (en) | 2018-07-04 | 2018-07-04 | A kind of method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product |
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| CN108774542A true CN108774542A (en) | 2018-11-09 |
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| CN201810725218.1A Pending CN108774542A (en) | 2018-07-04 | 2018-07-04 | A kind of method that mononuclear phenolic compound hydrogenation deoxidation prepares hydro carbons in Catalytic lignin depolymerization product |
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| CN110128247A (en) * | 2019-05-23 | 2019-08-16 | 南京林业大学 | A kind of method of catalytic lignin depolymerization |
| WO2023184037A1 (en) * | 2022-04-01 | 2023-10-05 | Sixring Inc. | Method to manufacture biofuel |
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| WO2012083236A3 (en) * | 2010-12-16 | 2012-10-26 | Energia Technologies, Inc. | Catalysts, methods of preparation of catalyst, methods of deoxygenation, and systems for fuel production |
| CN104254418A (en) * | 2011-11-03 | 2014-12-31 | 克拉里安特国际有限公司 | Method for producing a metal nanoparticle dispersion, metal nanoparticle dispersion, and use of said metal nanoparticle dispersion |
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| WO2012083236A3 (en) * | 2010-12-16 | 2012-10-26 | Energia Technologies, Inc. | Catalysts, methods of preparation of catalyst, methods of deoxygenation, and systems for fuel production |
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Cited By (3)
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| CN110128247A (en) * | 2019-05-23 | 2019-08-16 | 南京林业大学 | A kind of method of catalytic lignin depolymerization |
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| WO2023184037A1 (en) * | 2022-04-01 | 2023-10-05 | Sixring Inc. | Method to manufacture biofuel |
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